#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:44:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180313 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/27/7152790.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7152790
loop_
_publ_author_name
'Niu, Teng-Fei'
'Lv, Mei-Fang'
'Wang, Liang'
'Yi, Wen-Bin'
'Cai, Chun'
_publ_section_title
;
 Chemoselective preparation of 1,2,3-triazole-isoxazole bisfunctional
 derivatives and their application in peptidomimetic synthesis.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1040
_journal_page_last               1048
_journal_paper_doi               10.1039/c2ob26990b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C20 H16 Cl N5 O2'
_chemical_formula_weight         393.83
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.469(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.877(6)
_cell_length_b                   9.516(3)
_cell_length_c                   10.966(3)
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.28
_cell_volume                     1864.9(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9134
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1404P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.2089
_reflns_number_gt                2358
_reflns_number_total             3218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26990b.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1864.8(10)
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7152790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.31454(15) 0.3292(3) -0.3288(3) 0.0642(8) Uani 1 1 d .
C2 C 1.30703(16) 0.4411(4) -0.2511(3) 0.0699(9) Uani 1 1 d .
H2 H 1.3380 0.5191 -0.2579 0.084 Uiso 1 1 calc R
C3 C 1.25355(15) 0.4378(3) -0.1628(3) 0.0601(8) Uani 1 1 d .
H3 H 1.2484 0.5131 -0.1096 0.072 Uiso 1 1 calc R
C4 C 1.20744(13) 0.3212(3) -0.1541(3) 0.0481(6) Uani 1 1 d .
C5 C 1.21593(15) 0.2092(3) -0.2322(3) 0.0543(7) Uani 1 1 d .
H5 H 1.1849 0.1312 -0.2264 0.065 Uiso 1 1 calc R
C6 C 1.26995(16) 0.2127(3) -0.3184(3) 0.0623(8) Uani 1 1 d .
H6 H 1.2764 0.1362 -0.3698 0.075 Uiso 1 1 calc R
C7 C 1.12204(12) 0.2147(2) 0.0006(2) 0.0425(6) Uani 1 1 d .
C8 C 1.14455(16) 0.0648(2) -0.0053(3) 0.0612(8) Uani 1 1 d .
H8A H 1.1381 0.0216 0.0728 0.092 Uiso 1 1 calc R
H8B H 1.1961 0.0586 -0.0270 0.092 Uiso 1 1 calc R
H8C H 1.1140 0.0172 -0.0656 0.092 Uiso 1 1 calc R
C9 C 1.07283(12) 0.2798(2) 0.0758(2) 0.0415(6) Uani 1 1 d .
C10 C 1.02549(12) 0.2162(2) 0.1682(2) 0.0433(6) Uani 1 1 d .
C11 C 0.94425(13) 0.2561(3) 0.3378(2) 0.0469(6) Uani 1 1 d .
H11A H 0.9484 0.3235 0.4039 0.056 Uiso 1 1 calc R
H11B H 0.9649 0.1678 0.3674 0.056 Uiso 1 1 calc R
C12 C 0.86337(13) 0.2347(2) 0.3065(2) 0.0401(6) Uani 1 1 d .
C13 C 0.80255(13) 0.2286(3) 0.3743(2) 0.0475(6) Uani 1 1 d .
H13 H 0.7997 0.2454 0.4576 0.057 Uiso 1 1 calc R
C14 C 0.74353(13) 0.1914(3) 0.2931(2) 0.0451(6) Uani 1 1 d .
C15 C 0.66409(14) 0.1664(3) 0.3197(3) 0.0518(7) Uani 1 1 d .
C16 C 0.63477(18) 0.2157(4) 0.4257(3) 0.0730(9) Uani 1 1 d .
H16 H 0.6653 0.2644 0.4811 0.088 Uiso 1 1 calc R
C17 C 0.56098(19) 0.1940(5) 0.4513(4) 0.0986(13) Uani 1 1 d .
H17 H 0.5417 0.2299 0.5228 0.118 Uiso 1 1 calc R
C18 C 0.5162(2) 0.1211(5) 0.3732(5) 0.1051(14) Uani 1 1 d .
H18 H 0.4661 0.1069 0.3910 0.126 Uiso 1 1 calc R
C19 C 0.54467(19) 0.0674(5) 0.2668(4) 0.0965(13) Uani 1 1 d .
H19 H 0.5139 0.0164 0.2134 0.116 Uiso 1 1 calc R
C20 C 0.61908(17) 0.0898(3) 0.2396(3) 0.0720(9) Uani 1 1 d .
H20 H 0.6385 0.0536 0.1682 0.086 Uiso 1 1 calc R
Cl1 Cl 1.37966(5) 0.33601(13) -0.44283(10) 0.1004(5) Uani 1 1 d .
N1 N 1.15138(11) 0.3205(2) -0.0642(2) 0.0466(6) Uani 1 1 d .
N2 N 1.12205(12) 0.4477(2) -0.0292(2) 0.0566(6) Uani 1 1 d .
N3 N 1.07487(12) 0.4207(2) 0.0560(2) 0.0515(6) Uani 1 1 d .
N4 N 0.98861(11) 0.3045(2) 0.2391(2) 0.0480(6) Uani 1 1 d .
H4 H 0.9915 0.3933 0.2253 0.058 Uiso 1 1 calc R
N5 N 0.76719(12) 0.1786(3) 0.1817(2) 0.0613(7) Uani 1 1 d .
O1 O 1.02220(11) 0.08771(17) 0.17992(19) 0.0635(6) Uani 1 1 d .
O2 O 0.84458(10) 0.2062(2) 0.18973(17) 0.0580(6) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.5(3)
C6 C1 Cl1 119.6(3)
C2 C1 Cl1 119.8(2)
C1 C2 C3 119.9(3)
C1 C2 H2 120.0
C3 C2 H2 120.0
C2 C3 C4 119.4(3)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 120.0(3)
C5 C4 N1 121.2(2)
C3 C4 N1 118.8(2)
C6 C5 C4 120.1(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 120.0(3)
C5 C6 H6 120.0
C1 C6 H6 120.0
N1 C7 C9 104.11(19)
N1 C7 C8 125.9(2)
C9 C7 C8 129.8(2)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N3 C9 C7 109.3(2)
N3 C9 C10 122.4(2)
C7 C9 C10 128.3(2)
O1 C10 N4 122.7(2)
O1 C10 C9 120.8(2)
N4 C10 C9 116.5(2)
N4 C11 C12 115.0(2)
N4 C11 H11A 108.5
C12 C11 H11A 108.5
N4 C11 H11B 108.5
C12 C11 H11B 108.5
H11A C11 H11B 107.5
C13 C12 O2 109.6(2)
C13 C12 C11 132.6(2)
O2 C12 C11 117.6(2)
C12 C13 C14 105.5(2)
C12 C13 H13 127.3
C14 C13 H13 127.3
N5 C14 C13 111.0(2)
N5 C14 C15 120.3(2)
C13 C14 C15 128.7(3)
C16 C15 C20 119.4(3)
C16 C15 C14 120.2(3)
C20 C15 C14 120.4(3)
C15 C16 C17 120.9(3)
C15 C16 H16 119.6
C17 C16 H16 119.6
C18 C17 C16 120.4(4)
C18 C17 H17 119.8
C16 C17 H17 119.8
C17 C18 C19 119.9(4)
C17 C18 H18 120.0
C19 C18 H18 120.0
C18 C19 C20 120.1(4)
C18 C19 H19 120.0
C20 C19 H19 120.0
C15 C20 C19 119.3(3)
C15 C20 H20 120.4
C19 C20 H20 120.4
C7 N1 N2 110.7(2)
C7 N1 C4 131.2(2)
N2 N1 C4 117.96(19)
N3 N2 N1 106.61(19)
N2 N3 C9 109.3(2)
C10 N4 C11 122.0(2)
C10 N4 H4 119.0
C11 N4 H4 119.0
C14 N5 O2 105.4(2)
C12 O2 N5 108.56(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.371(5)
C1 C2 1.374(5)
C1 Cl1 1.731(3)
C2 C3 1.378(4)
C2 H2 0.9300
C3 C4 1.387(4)
C3 H3 0.9300
C4 C5 1.378(4)
C4 N1 1.424(3)
C5 C6 1.368(4)
C5 H5 0.9300
C6 H6 0.9300
C7 N1 1.347(3)
C7 C9 1.370(3)
C7 C8 1.484(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 N3 1.359(3)
C9 C10 1.468(3)
C10 O1 1.231(3)
C10 N4 1.331(3)
C11 N4 1.434(3)
C11 C12 1.491(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.334(3)
C12 O2 1.343(3)
C13 C14 1.408(3)
C13 H13 0.9300
C14 N5 1.309(4)
C14 C15 1.476(4)
C15 C16 1.370(4)
C15 C20 1.384(4)
C16 C17 1.371(4)
C16 H16 0.9300
C17 C18 1.349(6)
C17 H17 0.9300
C18 C19 1.383(6)
C18 H18 0.9300
C19 C20 1.387(5)
C19 H19 0.9300
C20 H20 0.9300
N1 N2 1.377(3)
N2 N3 1.300(3)
N4 H4 0.8600
N5 O2 1.409(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -1.0(4)
Cl1 C1 C2 C3 177.9(2)
C1 C2 C3 C4 -0.4(4)
C2 C3 C4 C5 0.8(4)
C2 C3 C4 N1 -178.7(2)
C3 C4 C5 C6 0.1(4)
N1 C4 C5 C6 179.6(2)
C4 C5 C6 C1 -1.5(4)
C2 C1 C6 C5 2.0(4)
Cl1 C1 C6 C5 -176.9(2)
N1 C7 C9 N3 -1.0(2)
C8 C7 C9 N3 174.5(3)
N1 C7 C9 C10 -179.0(2)
C8 C7 C9 C10 -3.5(4)
N3 C9 C10 O1 176.5(2)
C7 C9 C10 O1 -5.8(4)
N3 C9 C10 N4 -5.1(3)
C7 C9 C10 N4 172.6(2)
N4 C11 C12 C13 -159.0(2)
N4 C11 C12 O2 26.2(3)
O2 C12 C13 C14 1.1(3)
C11 C12 C13 C14 -174.0(2)
C12 C13 C14 N5 -1.3(3)
C12 C13 C14 C15 178.3(2)
N5 C14 C15 C16 -162.0(3)
C13 C14 C15 C16 18.4(4)
N5 C14 C15 C20 19.8(4)
C13 C14 C15 C20 -159.7(3)
C20 C15 C16 C17 -2.2(5)
C14 C15 C16 C17 179.6(3)
C15 C16 C17 C18 1.4(7)
C16 C17 C18 C19 0.1(8)
C17 C18 C19 C20 -0.6(7)
C16 C15 C20 C19 1.6(5)
C14 C15 C20 C19 179.8(3)
C18 C19 C20 C15 -0.2(6)
C9 C7 N1 N2 0.8(3)
C8 C7 N1 N2 -175.0(2)
C9 C7 N1 C4 177.6(2)
C8 C7 N1 C4 1.8(4)
C5 C4 N1 C7 32.7(4)
C3 C4 N1 C7 -147.8(3)
C5 C4 N1 N2 -150.6(2)
C3 C4 N1 N2 28.9(3)
C7 N1 N2 N3 -0.2(3)
C4 N1 N2 N3 -177.5(2)
N1 N2 N3 C9 -0.4(3)
C7 C9 N3 N2 0.9(3)
C10 C9 N3 N2 179.1(2)
O1 C10 N4 C11 2.3(4)
C9 C10 N4 C11 -176.0(2)
C12 C11 N4 C10 -93.6(3)
C13 C14 N5 O2 0.9(3)
C15 C14 N5 O2 -178.7(2)
C13 C12 O2 N5 -0.6(3)
C11 C12 O2 N5 175.3(2)
C14 N5 O2 C12 -0.2(3)
